Patent GB-850311-A (GB)
Title: Aralkyl esters of unsaturated monocarboxylic acids and polymeric compositions obtained therefrom
IPC: C08F20/18
Filed: 1957-01-01
Abstract: The invention comprises polymeric compounds derived from monomers of formula (R-R1)n-Ar wherein R is the radical derived by the removal of the carboxyl hydrogen atom from an alpha, beta-ethylenically unsaturated monocarboxylic acid, R1 is an alkylene radical, n is 1 or 2 and Ar is a phenyl radical having at least two ring substituents other than an (R-R1) group, said substituents being alkyl or haloalkyl radicals having from 1-4 carbon atoms (see Group IV(b)). Specified monomers include dimethylbenzyl acrylate, 1:4-dimethyl -3:5- dimethacryloxymethyl-or-diacryloxymethyl - benzene, 1:4-dimethyl-3-chloromethyl - 5 - acryloxymethyl-ormethacryloxymethyl-benzene, and 1:4-dimethyl-3-acryloxymethyl-5- methacryloxymethylbenzene.  The monomers may be used to prepare homopolymers and also interpolymers by copolymerisation with other monomers such as olefinic hydrocarbons, halo-olefinic hydrocarbons, alkenyl nitriles and unsaturated esters, acids and amides.  The polymerisation is carried out in bulk, in solution or by emulsion or bead methods using inorganic or organic peroxidic compounds or diazo compounds as catalysts.  In examples the polymerisation of the following monomers or mixtures thereof is specified: dimethylbenzyl methacrylate; 1:5-dimethyl - 2:4 - dimethacryloxymethyl- and -diacryloxymethylbenzenes; 1:5-dimethyl - 2:4 - dimethacryloxymethylbenzene and methyl methacrylate or dimethyl methacrylate; 1:5-dimethyl - 2:4-dimethacryloxymethyl benzene, dimethylbenzyl methacrylate and triallyl cyanurate; 1:5-dimethyl-2:4-dimethacryloxymethylbenzene, dimethylbenzyl methacrylate and triallyl cyanurate with or without allyl methacrylate; dimethylbenzyl methacrylate, acrylamide and ethyl acrylate are copolymerised in butanol solution and the mixture reacted further with a butanol solution of formaldehyde and maleic anhydride to give a film-forming resin (see Group III); dimethylbenzyl methacrylate, styrene and propylene maleate phthalate polyester, diethylene glycol bis (allyl carbonate), 1:5 dimethyl-2:4-dimethacryloxymethylbenzene, dimethylbenzyl methacrylate, methyl methacrylate and diallyl itaconate.ALSO:The invention comprises compounds of formula: (R-R1)n-Ar wherein R is the radical derived by the removal of the carboxyl hydrogen atom from an alpha, beta-ethylenically unsaturated monocarboxylic acid, R1 is an alkylene radical, n is 1 or 2 and Ar is a phenyl radical having at least two ring substituents other than an (R-R1) group, said ring substituents being alkyl or haloalkyl radicals having from one to four carbon atoms.  The compounds are used to form polymeric compositions (see Group IV(a)).  They are prepared by reacting the corresponding mono- or dihaloalkyl-benzenes with salts of alpha, beta-unsaturated acids.  Specified acids are acrylic, methacrylic, 2-butenoic, 2-methyl-2-propenoic and oleic. In an Example a mixture of monochloromethyl-p-xylene, potassium methacrylate, hydroquinone, methacrylic acid, and dimethylformamide is refluxed, potassium chloride is filtered off, the filtrate is washed with dimethyl formamide and water and the product extracted with toluene.  The toluene layer is washed with water, dried and distilled in vacuo to give 2 : 5-dimethylbenzyl methacrylate.  Further compounds prepared similarly are 1 : 4-dimethyl-3 : 5-dimethacryloxymethyl-benzene, dimethylbenzyl acrylate (mixture of isomers) and 1 : 5-dimethyl-2 : 4-diacryloxymethyl-benzene.  Further compounds specified are 1 : 4-dimethyl-3-chloromethyl-5-acryloxymethyl-or-methacryloxymethyl benzene, 1 : 4-dimethyl-3 : 5-diacryloxymethylbenzene and 1 : 4-dimethyl-3-acryloxymethyl-5-methacryloxymethyl-benzene.ALSO:Steel and glass plates are coated with a resin composition obtained by copolymerizing dimethylbenzyl methacrylate, acrylamide and ethyl acrylate in butanol solution and treating the mixture obtained with a butanol solution of formaldehyde and maleic anhydride and the films baked.  The composition can be pigmented with titanium dioxide.